Quality Connections Take Time

Need dating advice, to meet dates or just short on time?

This is exactly where a professional introduction service and dating coaching can benefit you!

Don't let five minutes stand between you and a meaningful connection!

Chicago Matchmaking Services

Chicago matchmaker Stef, at Stef and the City is an alternative to costly introduction services that might not have the types of people you are looking for. We have the BEST prices among Chicago dating services, and offer the BEST options for singles. It’s personalized matchmaking! Not only do we have a great base of clients, but we also continually search for new clients that fit what our clients are looking for.

We continue to bring new people into our service on a daily basis! Whether it’s having our staff go out and about, our constant publicity, or world of mouth- we get NEW people coming in daily to make our service successful! We believe in honesty about what we can provide for you and the timeline that it takes to do so. We would rather wait or search for you than to give you the wrong matches.

Dating these days is HARD. Ask yourself these questions to see if you may benefit from our Chicago Matchmaking Services:

  • Are you using only dating apps and getting ghosted on?
  • Has it been months since you’ve last had a GOOD date?
  • Are you spending too much time and not enough results?
  • Do you find that it’s hard to find attractive, quality singles?
  • Are you tired of meeting people that don’t look like their pictures?
  • Are you tired of being "ghosted" on?
  • Do you want to start go on dates for more than just coffee?
  • Do you need a new selection of people to meet?
  • Are you finding that you don’t know the “new” dating rules?
  • Are you in a dating rut?
  • Has it gotten a lot harder to meet people since you graduated college and since your friends have
    gotten married?
  • Did you recently get divorced and need to get help to get back into dating?
  • Do you feel like you are spending time seeking out dates and not getting anywhere?
  • Do the people you meet not the quality professional people you are looking for?
  • Are you looking for people that are serious about finding a long-term relationship?
  • Do you find that your social life needs a boost?

Our Process

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Our introduction service stays true to what people need- your own personal recruiter for dating!

  • We vet, screen, and interview each and every person you meet!
  • We invest the time and energy and get you the results you are looking for!
  • We give you the feedback that can make you even more successful in your relationships!
  • Let us find you the next love of your life!
    What do you have to lose?
  • Fill out our five minute questionnaire today!

Gentleman, we know you are looking for a two-way street in dating! Meet local amazing single women who are also invested emotionally and financially in meeting YOU!

Let us do the work!

Meeting attractive, quality, single women has never been so easy!

Our Services

We are MORE than just an introduction service. Be sure to check out all we have to offer.

  • Matchmaking: We do our specialized, screened matchmaking for both men and women!
  • Dating Coaching: New into dating after a long time? Gone through a recent divorce? Unsure why you are not getting the results you want? Get your own dating advisor.
  • Personalized Social Calendars: Maximize your time by getting assistance with personal life planning. Be where you need to be to meet the people that fit YOUR needs for relationships and friendships.
  • Events: We know where to go! As seen on ABC7, CBS2, NBC5, WCIU’s “You and Me This Morning”, Fox32, WGNWindy City Live and more we tell about the places to be at along with special Stef and the City discounts!
  • Singles Travel: Do you need to find places to travel that you are not the only single person? Do you want to travel internationally or abroad? We have the BEST prices and know the 411 on what you need to know!

We get new leads daily.  If we don't have a match for you today, you never know who we might meet for you tomorrow!

We cater to MANY age groups: It doesn't matter whether you are single and never married, divorced or widowed in your 20’s, 30’s, 40’s or 50’s, 60's- we have the people you want to meet!

Check out our Casting Call  page- we have new singles listed monthly.

We may already have your match!

As Seen On

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